Enantioselective single-crystal-to-single- crystal photodimerization of coumarin and thiocoumarin in inclusion complexes with chiral host compounds

Angewandte Chemie - International Edition

Volumn 38, Issue 23, 1999, Pages 3523-3525

  Tanaka, Koichi ^a   Toda, Fumio ^a   Mochizuki, Eiko ^b   Yasui, Nobuyoshi ^b   Kai, Yasushi ^b   Miyahara, Ikuko ^c   Hirotsu, Ken ^c  

^a EHIME UNIVERSITY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

^c Osaka Prefecture University   (Japan)

Author keywords

Asymmetric synthesis; Dimerizations; Host guest chemistry; Photochemistry; Solid state chemistry

Indexed keywords

COUMARIN; COUMARIN DERIVATIVE; CYCLOBUTANE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; DIMERIZATION; ENANTIOMER; PHOTOREACTIVITY; X RAY DIFFRACTION;

EID: 0033521193     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991203)38:23<3523::AID-ANIE3523>3.0.CO;2-G     Document Type: Article

References (16)

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10. max = 59.5°. All the crystallographic calculations were performed using the TEXSAN software package of the Molecular Structure Corporation. The crystal structures were solved by direct methods and refined by full-matrix least squares. All non-hydrogen atoms and hydrogen atoms were refined anisotropically and isotropically, respectively.
11. 3. Data collection and analysis were carried out in a similar way to those for 4.
12. K. Tanaka, F. Toda, Mol. Cryst. Liq. Cryst. 1998, 313, 179-184; C. P. Klaus, C. Thiemann, J. Kopf, P. Margaretha, Helv. Chim. Acta. 1995, 78, 1079-1082; J. Kopf, H. Maelger, C. Thiemann, P. Margaretha, Acta Crystallogr. Sect. C 1994, 50, 1922-1924.
13. K. Tanaka, F. Toda, Mol. Cryst. Liq. Cryst. 1998, 313, 179-184; C. P. Klaus, C. Thiemann, J. Kopf, P. Margaretha, Helv. Chim. Acta. 1995, 78, 1079-1082; J. Kopf, H. Maelger, C. Thiemann, P. Margaretha, Acta Crystallogr. Sect. C 1994, 50, 1922-1924.
14. K. Tanaka, F. Toda, Mol. Cryst. Liq. Cryst. 1998, 313, 179-184; C. P. Klaus, C. Thiemann, J. Kopf, P. Margaretha, Helv. Chim. Acta. 1995, 78, 1079-1082; J. Kopf, H. Maelger, C. Thiemann, P. Margaretha, Acta Crystallogr. Sect. C 1994, 50, 1922-1924.
15. The optical purity was determined by HPLC on a chiral stationary phase (Chiralpak AS column; Daicel Chemical Co. Ltd., Himeji (Japan). The lactone ring of 3a in complex 5 was opened by acid catalyzed esterification and the optical purity of the total reaction determined as 96% ee by HPLC.
16. Crystallographic Data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-118773(4) and -118774(5). Copies of the data can be obtained free of charge on application to CCDC, 12 union Road, Cambridge CB2 1EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam. ac.uk)